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United States Patent |
5,158,850
|
Sasaki
,   et al.
|
October 27, 1992
|
Polyether compounds and electrophotographic photoconductor comprising
one polyether compound
Abstract
An electrophotographic photoconductor comprising an electroconductive
support and a photoconductive layer formed thereon comprising as an
effective component at least one polyether compound represented by formula
(I):
##STR1##
wherein Ar represents a phenylene group or a biphenylene group; R.sup.1
and R.sup.2 each represent an alkyl group which may have a substituent, or
an aryl group which may have a substituent; and n is an integer of 1 to 4.
Furthermore, charge transporting material comprising the above polyether
compound, polyether compounds having formula (II) for use in the
electrophotographic photoconductor and a method of preparing the same are
disclosed,
##STR2##
wherein m is an integer of 1 or 2.
Inventors:
|
Sasaki; Masaomi (Susono, JP);
Aruga; Tamotsu (Mishima, JP);
Shimada; Tomoyuki (Numazu, JP)
|
Assignee:
|
Ricoh Company, Ltd. (Tokyo, JP)
|
Appl. No.:
|
626906 |
Filed:
|
December 13, 1990 |
Foreign Application Priority Data
| Dec 15, 1989[JP] | 1-325409 |
| Dec 28, 1989[JP] | 1-342793 |
Current U.S. Class: |
430/71; 430/58.5; 430/58.75; 430/72; 430/73; 430/74 |
Intern'l Class: |
G03G 005/06 |
Field of Search: |
430/74,901,59,71,72,73
564/434,347
|
References Cited
U.S. Patent Documents
4665000 | May., 1987 | Tokoli et al. | 430/59.
|
4931350 | Jun., 1990 | Shimada et al. | 430/59.
|
Foreign Patent Documents |
2608082 | Sep., 1976 | DE | 430/74.
|
56-142535 | Nov., 1981 | JP | 430/74.
|
Primary Examiner: McCamish; Marion E.
Assistant Examiner: RoDee; Christopher D.
Attorney, Agent or Firm: Oblon, Spivak, McClelland, Maier & Neustadt
Claims
What is claimed is:
1. An electrophotographic photoconductor comprising an electroconductive
support and a photoconductive layer formed thereon comprising as an
effective component at least one polyether compound represented by formula
(I):
##STR60##
wherein Ar represents a phenylene group or a biphenylene group; R.sup.1
and R.sup.2 each represent an alkyl group which may have a substituent, or
an aryl group which may have a substituent; and n is an integer of 1 to 4.
2. The electrophotographic photoconductor as claimed in claim 1, wherein
said aryl group is an aromatic group selected from the group consisting of
a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.
3. The electrophotographic photoconductor as claimed in claim 1, wherein
said substituent of said aryl group in formula (I) is selected from the
group consisting of:
(1) a halogen, a cyano group and a nitro group;
(2) an alkyl group, which may have a substituent selected from the group
consisting of a fluorine atom, an hydroxyl group, a cyano group, an alkoxy
group having 1 to 4 carbon atoms, and a phenyl group which may have a
substituent selected from the group consisting of a halogen, an alkyl
group having 1 to 4 carbon atoms, a 4-phenyl group and an alkoxy group
having 1 to 4 carbon atoms;
(3) an alkoxyl group represented by --OR.sup.3, in which R.sup.3 represents
said alkyl group which may have a substituent, as defined in (2);
(4) an aryloxy group, in which an aryl group represents a phenyl group or
naphthyl group, which aryloxy group may have a substituent selected from
the group consisting of an alkoxyl group having 1 to 4 carbon atoms, an
alkyl group having 1 to 4 carbon atoms and a halogen;
(5) a mercapto group represented by --SR.sup.4, in which R.sup.4 represents
said alkyl group which may have a substituent, as defined in (2) a phenyl
group or a p-methylphenyl group;
(6)
##STR61##
in which R.sup.5 and R.sup.6 independently represent hydrogen, said alkyl
group which may have a substituent, as defined in (2), aryl group, or
R.sup.5 and R.sup.6 together form a piperidino group, morpholino group or
julolidyl group; and
(7) an alkylenedioxy group and alkylenedithio group.
4. The electrophotographic photoconductor as claimed in claim 3, wherein
said alkyl group which may have a substituent is a straight-chain alkyl
group having 1 to 12 carbon atoms.
5. The electrophotographic photoconductor as claimed in claim 3, wherein
said alkyl group which may have a substituent is a branched-chain alkyl
group having 1 to 12 carbon atoms.
6. The electrophotographic photoconductor as claimed in claim 3, wherein
said alkyl group which may have a substituent is selected from the group
consisting of a methyl group, ethyl group, n-propyl group, i-propyl group,
t-butyl group, s-butyl group, n-butyl group, i-butyl group,
trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group,
2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl
group, 4-methylbenzyl group, 4-methoxybenzyl group and 4-phenylbenzyl
group.
7. The electrophotographic photoconductor as claimed in claim 3, wherein
said alkoxyl group --OR.sup.3 is selected from the group consisting of a
methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy
group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy
group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group and
trifluoromethoxy group.
8. The electrophotographic photoconductor as claimed in claim 3, wherein
said aryloxy group is selected from the group consisting of a phenoxy
group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group,
4-methoxyphenoxy group, 4-chlorophenoxy group and 6-methyl-2-naphthyloxy
group.
9. The electrophotographic photoconductor as claimed in claim 3, wherein
said mercapto group --SR.sup.4 is selected from the group consisting of a
methylthio group, ethylthio group, phenylthio group and p-methylphenylthio
group.
10. The electrophotographic photoconductor as claimed in claim 3, wherein
said aryl group represented by R.sup.5 or R.sup.6 is selected from the
group consisting of a phenyl group, biphenyl group and naphthyl group.
11. The electrophotographic photoconductor as claimed in claim 10, wherein
said aryl group may have a substituent selected from the group consisting
of an alkoxyl group having 1 to 4 carbon atoms, an alkyl group having 1 to
4 carbon atoms and a halogen.
12. The electrophotographic photoconductor as claimed in claim 3, wherein
the --NR.sup.5 R.sup.6 group is an amino group, diethylamino group,
N-methyl-N-phenylamino group, N,N-diphenylamino group,
N,N-di(p-tolyl)amino group, dibenzylamino group or R.sup.5 and R.sup.6 of
said
##STR62##
together form a piperidino group, morpholino group or julolidyl group.
13. The electrophotographic photoconductor as claimed in claim 3, wherein
said alkylenedioxy group or alkylenedithio group is selected from the
group consisting of a methylenedioxy group and methylenedithio group.
14. The electrophotographic photoconductor as claimed in claim 1, wherein
said alkyl group in formula (I) may have a substituent selected from the
group consisting of a fluorine atom, an hydroxyl group, a cyano group, an
alkoxyl group having 1 to 4 carbon atoms, and a phenyl group which may
have a substituent which is selected from the group consisting of a
halogen, an alkyl group having 1 to 4 carbon atoms, 4-phenyl and an alkoxy
group having 1 to 4 carbon atoms.
15. The electrophotographic photoconductor as claimed in claim 14, wherein
said alkyl group which may have a substituent is a straight-chain alkyl
group having 1 to 12 carbon atoms.
16. The electrophotographic photoconductor as claimed in claim 14, wherein
said alkyl group which may have a substituent is a branched-chain alkyl
group having 1 to 12 carbon atoms.
17. The electrophotographic photoconductor as claimed in claim 14, wherein
said alkyl group which may have a substituent is selected from the group
consisting of a methyl group, ethyl group, n-propyl group, i-propyl group,
t-butyl group, s-butyl group, n-butyl group, i-butyl group,
trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group,
2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl
group, 4-methylbenzyl group, 4-methoxybenzyl group and 4-phenylbenzyl
group.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to polyether compounds and an
electrophotographic photoconductor comprising a photoconductive layer
containing one polyether compound overlaid on an electrocoundutive
support.
2. Discussion of Background
Conventionally, inorganic materials such as selenium, cadmium sulfide and
zinc oxide are used as a photoconductive material of an
electrophotographic photoconductor in the electrophotographic process. The
above-mentioned electrophotographic process is one of the image forming
processes, through which the surface of the photoconductor is charged
uniformly in the dark to a predetermined polarity, for instance, by corona
charge. The uniformly charged photoconductor is exposed to a light image
to selectively dissipate the electrical charge of the exposed areas, so
that a latent electrostatic image is formed on the photoconductor. The
thus formed latent electrostatic image is developed by a developer
comprising a coloring agent such as a dye and a pigment, and a binder
agent such as a polymeric material, to a visible image.
Fundamental characteristics required for the photoconductor for in such an
electrophotographic process are: (1) chargeability to an appropriate
potential in the dark, (2) minimum dissipation of electrical charge in the
dark, and (3) rapid dissipation of electrical charge when exposed to
light.
However, while the above-mentioned inorganic materials have many
advantages, they have several shortcomings from the viewpoint of practical
use.
For instance, a selenium photoconductor, which is widely used at present,
satisfies the above-mentioned requirements (1) to (3) completely, but it
has the shortcomings that its manufacturing conditions are difficult and,
accordingly, its production cost is high. In addition, it is difficult to
work it into the form of a belt due to its poor flexibility, and it is so
vulnerable to heat and mechanical shocks that it must be handled with the
utmost care.
A cadmium sulfide photoconductor and a zinc oxide photoconductor can be
easily obtained by coating a dispersion of cadmium sulfide particles and
zinc oxide particles in a binder resin on a support. However, they are
poor in mechanical properties, such as surface smoothness, hardness,
tensile strength and wear resistance. Therefore, they cannot be used in
the repeated operation, as they are.
To solve the problems of the inorganic materials, various
electrophotographic photoconductors employing organic materials are
proposed recently and some are still put to practical use. For example,
there are known a photoconductor comprising poly-N-vinylcarbazole and
2,4,7-trinitrofluorene-9-on, as disclosed in U.S. Pat. No. 3,484,237; a
photoconductor prepared by sensitizing poly-N-vinylcarbazole with a
pigment of pyrylium salt, as described in Japanese Patent Publication
48-25658; a photoconductor comprising as the main component an organic
pigment, as described in Japanese Laid-Open Patent Application 47-37543; a
photoconductor comprising as the main component an eutectic crystal
complex of a dye and a resin, as described in Japanese Laid-Open Patent
Application 47-10735; a photoconductor prepared by sensitizing a
triphenylamine compound with a sensitizer pigment, as described in U.S.
Pat. No. 3,180,730; a photoconductor comprising an amine derivative as a
charge transporting material, as described in Japanese Laid-Open Patent
Application 57-195254; a photoconductor comprising poly-N-vinylcarbazole
and an amine derivative as charge transporting materials, as described in
Japanese Laid-Open Patent Application 58-1155; and a photoconductor
comprising a polyfunctional tertiary amine compound, in particular
benzidine compound, as a photoconductive material, as described in U.S.
Pat. No. 3,265,496, Japanese Patent Publication 39-11546 and Japanese
Laid-Open Patent Application 53-27033.
These electrophotographic photoconductors have their own excellent
characteristics and considered to be valuable for practical use. With
various requirements of the electrophotographic photoconductor in
electrophotography taken into consideration, however, the above-mentioned
conventional electrophotographic photoconductors cannot meet all the
requirements for use in electrophotography.
SUMMARY OF THE INVENTION
It is therefore a first object of the present invention to privide an
electrophotographic photoconductor free from the conventional
shortcomings, which can completely satisfy all the requirements in the
electrophotographic process, including high durability, and can be easily
manufactured at relatively low cost.
A second object of the present invention is to provide a photoconductive
material for use in the above-mentioned electrophotographic
photoconductor.
A third object of the present invention is to provide polyether compounds
employed as photoconductive materials in the electrophotographic
photoconductor.
A fourth object of the present invention is to provide intermediate
compounds for preparing the above polyether compounds.
A fifth object of the present invention is to provide a method of preparing
the above polyether compounds.
The first object of the present invention can be achieved by an
electrophotographic photoconductor comprising an electroconductive support
and a photoconductive layer formed thereon comprising as an effective
component at least one polyether compound represented by formula (I):
##STR3##
wherein Ar represents a phenylene group or a biphenylene group; R.sup.1
and R.sup.2 each represent an alkyl group which may have a substituent, or
an aryl group which may have a substituent; and n is an integer of 1 to 4.
The second object of the present invention can be achieved by a material
comprising a polyether compound represented by the above formula (I).
The third object of the present invention can be attained by polyether
compounds having formula (II):
##STR4##
wherein m is an integer of 1 or 2.
The fourth object of the present inventin can be achieved by 3-oxapentane
compounds having formula (III):
##STR5##
wherein m is an integer of 1 or 2.
The fifth object of the present invention is attained by subjecting a
3-oxapentane compound of formula (III) and a dimethyl diphenyl amine
derivative of formula (IV) to the Ullmann coupling reaction in the
following reaction scheme:
##STR6##
BRIEF DESCRIPTION OF THE DRAWINGS
A more complete appreciation of the invention and many of the attendant
advantages thereof will be readily obtained as the same becomes better
understood by reference to the following detailed description when
considered in connection with the accompanying drawings, wherein:
FIGS. 1 and 2 are the IR spectra of 3-oxapentane compounds, serving as the
intermediate materials for preparing the polyether compounds according to
the present invention;
FIG. 3 is an IR spectrum of an polyether compound according to the present
invention;
FIG. 4 is a schematic cross-sectional view of a first example of an
electrophotographic photoconductor according to the present invention;
FIG. 5 is a schematic cross-sectional view of a second example of an
electrophotographic photoconductor according to the present invention;
FIG. 6 is a schematic cross-sectional view of a third example of an
electrophotographic photoconductor according to the present invention;
FIG. 7 is a schematic cross-sectional view of a fourth example of an
electrophotographic photoconductor according to the present invention; and
FIG. 8 is a schematic cross-sectional view of a fifth example of an
electrophotographic photoconductor according to the present invention.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
An electrophotographic photoconductor according to the present invention
comprises an electroconductive support and a photoconductive layer formed
thereon, comprising at least one of polyether compounds of formula (I):
##STR7##
wherein Ar represents a phenylene group or a biphenylene group; R.sup.1
and R.sup.2 each represent an alkyl group which may have a substituent, or
an aryl group which may have a substituent; and n is an integer of 1 to 4.
When R.sup.1 and R.sup.2 each represent an aryl group, examples of the aryl
group include aromatic groups, such as a phenyl group, a biphenyl group, a
terphenyl group and a naphthyl group.
Examples of the substituent of the aryl group in the formula (I) are as
follows:
(1) A halogen, a cyano group and a nitro group.
(2) An alkyl group, in particular a straight-chain or branched-chain alkyl
group having 1 to 12 carbon atoms, more preferably an alkyl group having 1
to 8 carbon atoms, and further preferably an alkyl group having 1 to 4
carbon atoms. The above alkyl group may have a substituent such as a
fluorine atom, an hydroxyl group, a cyano group, an alkoxyl group having 1
to 4 carbon atoms, and a phenyl group which may have a substituent such as
a halogen, an alkyl group having 1 to 4 carbon atoms or an alkoxyl group
having 1 to 4 carbon atoms.
Specific examples of the above alkyl group include a methyl group, ethyl
group, n-propyl group, i-propyl group, t-butyl group, s-butyl group,
n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group,
2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl
group, 4-chlorobenzyl group, 4-methylbenzyl group, 4-methoxybenzyl group
and 4-phenylbenzyl group.
(3) An alkoxyl group represented by --OR.sup.3, in which R.sup.3 represents
the same alkyl group as defined in (2).
Specific examples of the above alkoxyl group include a methoxy group,
ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy
group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group,
2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group and
trifluoromethoxy group.
(4) An aryloxy group, in which an aryl group represents, for example, a
phenyl group and a naphthyl group. The above aryloxy group may have a
substituent such as an alkoxyl group having 1 to 4 carbon atoms, an alkyl
group having 1 to 4 carbon atoms or a halogen.
Specific examples of the above aryloxy group include a phenoxy group,
1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group,
4-methoxyphenoxy group, 4-chlorophenoxy group and 6-methyl-2-naphthyloxy
group.
(5) An alkylmercapto group represented by --SR.sup.4, in which R.sup.4
represents the same alkyl group as defined in (2).
Specific examples of the above alkylmercapto group include a methylthio
group, ethylthio group, phenylthio group and p-methylphenylthio group.
(6)
##STR8##
in which R.sup.5 and R.sup.6 independently represent hydrogen, the same
alkyl group as defined in (2) or aryl group. As the aryl group, a phenyl
group, biphenyl group or naphthyl group can be employed, which may have a
substituent such as an alkoxyl group having 1 to 4 carbon atoms, an alkyl
group having 1 to 4 carbon atoms or a halogen R.sup.5 and R.sup.6 may form
a ring in combination, or in combination with carbon atoms on the aryl
group.
Specific examples of the above
##STR9##
include an amino group, diethylamino group, N-methyl-N-phenylamino group,
N,N-diphenylamino group, N,N-di(p-tolyl)amino group, dibenzylamino group,
piperidino group, morpholino group and julolidyl group.
(7) An alkylenedioxy group or alkylenedithio group such as a methylenedioxy
group or methylenedithio group.
When R.sup.1 and R.sup.2 each represent an alkyl group in formula (I), the
same alkyl group as defined in the above (2) can be employed.
Specific examples of the polyether compounds according to the present
invention are shown in the following Table 1.
TABLE 1
__________________________________________________________________________
##STR10## (I)
Compound No.
Ar R.sup.1 R.sup.2 n
__________________________________________________________________________
1
##STR11##
##STR12##
##STR13## 1
2 " CH.sub.3
##STR14## 1
3 "
##STR15##
##STR16## 1
4 "
##STR17##
##STR18## 1
5 "
##STR19##
##STR20## 1
6 "
##STR21##
##STR22## 1
7 "
##STR23##
##STR24## 1
8 "
##STR25##
##STR26## 1
9 "
##STR27##
##STR28## 2
10 "
##STR29##
##STR30## 3
11 "
##STR31##
##STR32## 4
12
##STR33##
##STR34##
##STR35## 1
13 "
##STR36##
##STR37## 1
14 "
##STR38##
##STR39## 1
15 "
##STR40##
##STR41## 1
16 "
##STR42## CH.sub.3 1
17 "
##STR43##
##STR44## 2
18 "
##STR45##
##STR46## 3
__________________________________________________________________________
The polyether compounds of formula (I) according to the present invention
can be obtained by allowing a compound having formula (V) to react with a
halogenide having formula (VI).
##STR47##
wherein R.sup.1 and R.sup.2 are the same as previously defined in formula
(I).
X--Ar--OCH.sub.2 CH.sub.2 --(OCH.sub.2 CH.sub.2).sub.n --O--Ar--X(VI)
wherein Ar and n are the same as previously defined in formula (I), and X
represents a halogen.
More specifically, polyether compounds No. 4 and No. 12 in Table 1 can be
obtained by allowing a 3-oxapentane compound having formula (III) to react
with a dimethyldiphenylamine derivative of formula (IV) by the Ullmann
coupling reaction in accordance with the following reaction scheme:
##STR48##
Namely, a 3-oxapentane compound of formula (III) is allowed to react with a
dimethyldiphenylamine derivative of formula (IV) in a solvent in a stream
of nitrogen at about 150.degree. to 250.degree. C. in the presence of
copper particles, copper oxide or copper halogenide, with an alkaline salt
or alkaline material added thereto in a sufficient amount for neutralizing
hydrogen halogenide generated in the course of the reaction. In this case,
the solvent may not be used in the reaction.
Examples of the above-mentioned alkaline salt used in the reaction are
sodium carbonate and potassium carbonate; and examples of the alkaline
material are sodium hydroxide and other caustic alkaline materials.
Examples of the solvent used in the reaction are nitrobenzene,
dichlorobenzene, quinoline, N,N-dimethylformamide, dimethyl sulfoxide,
N-methylpyrrolidone and 1,3-dimethyl-2-imidazolidinone.
The above-mentioned 3-oxapentane compound of formula (III) can be prepared
by refluxing a mixture of a 1,5-dichloro-3-oxapentane and a compound
represented by the following formula (VII) in water or an organic solvent
in the presence of a caustic alkaline material such as sodium hydroxide
and potassium hydroxide. In this case, benzene, toluene,
N,N-dimethylformamide, dimethyl sulfoxide, ethanol and n-butanol can be
used as the above-mentioned organic solvent.
##STR49##
wherein m is an integer of 1 or 2.
The polyether compounds according to the present invention, which are
remarkably effective as photoconductive materials in the
electrophotographic photoconductor, are optically or chemically sensitized
with a sensitizer such as a dye or Lewis acid. In addition, the polyether
compounds effectively function as a charge transporting material in a
function-separating type electrophotographic photoconductor where an
organic or inorganic pigment serves as a charge generating material
In the photoconductors according to the present invention, at least one
polyether compound of the formula (I) is contained in the photoconductive
layers 2, 2a, 2b, 2c and 2d. The polyether compounds can be employed in
different ways, for example, as shown in FIGS. 4 through 8.
In the photoconductor as shown in FIG. 4, a photoconductive layer 2 is
formed on an electroconductive support 1, which photoconductive layer 2
comprises a polyether compound, a sensitizing dye and a binder agent
(binder resin). In this photoconductor, the polyether compound works as a
photoconductive material, through which charge carriers which are
necessary for the light decay of the photoconductor are generated and
transported. However, the polyether compound itself scarcely absorbs light
in the visible light range and, therefore, it is necessary to add a
sensitizing dye which absorbs light in the visible light range in order to
form latent electrostatic images by use of visible light.
Referring to FIG. 5, there is shown an enlarged cross-sectional view of
another embodiment of an electrophotographic photoconductor according to
the present invention. In the figure, reference numeral 1 indicates an
electroconductive support. On the electroconductive support 1, there is
formed a photoconductive layer 2a comprising a charge generating material
3 dispersed in a charge transporting medium 4 comprising a polyether
compound and a binder agent. In this embodiment, the polyether compound
and the binder agent (or a mixture of the binder agent and a plasticizer)
in combination constitute the charge transporting medium 4. The charge
generating material 3, which is, for example, an inorganic or organic
pigment, generates charge carriers The charge transporting medium 4
accepts the charge carriers generated by the charge generating material 3
and transports those charge carriers.
In this electrophotographic photoconductor, it is basically necessary that
the light-absorption wavelength regions of the charge generating material
3 and the polyether compound not overlap in the visible light range. This
is because, in order that the charge generating material 3 produce charge
carriers efficiently, it is necessary that light pass through the charge
transporting medium 4 and reach the surface of the charge generating
material 3. Since the polyether compounds of the previously described
general formula (I) do not substantially absorb light in the visible
range, they can work effectively as charge transporting materials in
combination with the charge generating material 3 which absorbs the light
in the visible region and generates charge carriers.
Referring to FIG. 6, there is shown an enlarged cross-sectional view of a
further embodiment of an electrophotographic photoconductor according to
the present invention. In the figure, there is formed on an
electroconductive support 1 a two-layered photoconductive layer 2b
comprising a charge generation layer 5 containing the charge generating
material 3, and a charge transport layer 4 containing a polyether compound
of the previously described formula (I).
In this photoconductor, light which has passed through the charge transport
layer 4 reaches the charge generation layer 5, and charge carriers are
generated within the charge generation layer 5. The charge carriers which
are necessary for the light decay for latent electrostatic image formation
are generated by the charge generating material 3, accepted and
transported by the charge transport layer 4. In the charge transport layer
4, the polyether compound mainly works for transporting charge carriers.
The generation and transportation of the charge carriers are performed by
the same mechanism as that in the photoconductor shown in FIG. 5.
Referring to FIG. 7, there is shown still another embodiment of an
electrophotographic photoconductor according to the present invention. In
the figure, the overlaying order of the charge generation layer 5 and the
charge transport layer 4 is reversed in view of the electrophotographic
photoconductor as shown in FIG. 6. The mechanism of the generation and
transportation of charge carriers is substantially the same as that of the
photoconductor shown in FIG. 6.
In the above photoconductor, a protective layer 6 may be formed on the
charge generation layer 5 as shown in FIG. 8 for protecting the charge
generation layer 5.
When the electrophotographic photoconductor according to the present
invention as shown in FIG. 4 is prepared, at least one polyether compound
of the previously described formula (I) is dispersed in a binder resin
solution, and a sensitizing dye is then added to the mixture, so that a
photoconductive layer coating liquid is prepared. The thus prepared
photoconductive layer coating liquid is coated on an electroconductive
support 1 and dried, so that a photoconductive layer 2 is formed on the
electroconductive support 1.
It is preferable that the thickness of the photoconductive layer 2 be in
the range of 3 to 50 .mu.m, more preferably in the range of 5 to 20 .mu.m.
It is preferable that the amount of the polyether compound contained in
the photoconductive layer 2 be in the range or 30 to 70 wt. %, more
preferably about 50 wt. %.
It is preferable that the amount of the sensitizing dye contained in the
photoconductive layer 2 be in the range of 0.1 to 5 wt. %, more preferably
in the range of 0.5 to 3 wt. %.
Specific examples of the sensitizing dye for use in the present invention
are: triarylmethane dyes such as Brilliant Green, Victoria Blue B, Methyl
Violet, Crystal Violet and Acid Violet 6B; xanthene dyes such as Rhodamine
B, Rhodamine 6G, Rhodamine G Extra, Eosin S, Erythrosin, Rose Bengale and
Fluoresceine; thiazine dyes such as Methylene Blue; cyanine dyes such as
cyanin; and pyrylium dyes such as
2,6-diphenyl-4-(N,N-dimethylaminophenyl)thiapyrylium perchlorate and
benzopyrylium salts (described in Japanese Patent Publication 48-25658).
These sensitizing dyes can be used alone or in combination.
The electrophotographic photoconductor shown in FIG. 5 can be obtained by
dispersing finely-divided particles of the charge generating material 3 in
the solution in which at least one polyether compound for use in the
present invention and the binder agent are dissolved, coating the
above-prepared dispersion on the electroconductive support 1 and then
drying the same to form the photoconductive layer 2a.
It is preferable that the thickness of the photoconductive layer 2a be in
the range of 3 to 50 .mu.m, more preferably in the range of 5 to 20 .mu.m.
It is preferable that the amount of the polyether compound contained in
the photoconductive layer 2a be in the range of 10 to 95 wt. %, more
preferably in the range of 30 to 90 wt. %.
It is preferable that the amount of the charge generating material 3
contained in the photoconductive layer 2a be in the range of 0.1 to 50 wt.
%, more preferably in the range of 1 to 20 wt. %.
Specific examples of the charge generating material 3 for use in the
present invention are as follows: inorganic pigments such as selenium,
selenium - tellurium, cadmium sulfide, cadmium sulfide - selenium and
.alpha.-silicone; and organic pigments, such as C.I. Pigment Blue 25 (C.I
21180), C.I. Pigment Red 41 (C.I. 21200), C.I. Acid Red 52 (C.I. 45100),
and C.I. Basic Red 3 (C.I. 45210); an azo pigment having a carbazole
skeleton (Japanese Laid-Open Patent Application 53-95033), an azo pigment
having a distyryl benzene skeleton (Japanese Laid-Open Patent Application
53-133445), an azo pigment having a triphenylamine skeleton (Japanese
Laid-Open Patent Application 53-132347), an azo pigment having a
dibenzothiophene skeleton (Japanese Laid-Open Patent Application
54-21728), an azo pigment having an oxadiazole skeleton (Japanese
Laid-Open Patent Application 54-12742), an azo pigment having a fluorenone
skeleton (Japanese Laid-Open Patent Application 54-22834), an azo pigment
having a bisstilbene skeleton (Japanese Laid-Open Patent Application
54-17733), an azo pigment having a distyryl oxadiazole skeleton (Japanese
Laid-Open Patent Application 54-2129), and an azo pigment having a
distyryl carbazole skeleton (Japanese Laid-Open Patent Application
54-14967); a phthalocyanine pigment such as C.I. Pigment Blue 16 (C.I.
74100); indigo pigments such as C.I. Vat Brown 5 (C.I. 73410) and C.I. Vat
Dye (C.I. 73030); and perylene pigments such as Algol Scarlet B and
Indanthrene Scarlet R (made by Bayer Co., Ltd.). These charge generating
materials may be used alone or in combination.
The electrophotographic photoconductor shown in FIG. 6 can be obtained as
follows:
The charge generating material is vacuum-deposited on the electroconductive
support 1, or the dispersion in which finely-divided particles of the
charge generating material 3 is dispersed in an appropriate solvent,
together with the binder agent when necessary, is coated on the
electroconductive support 1 and dried, so that the charge generation layer
5 is formed. When necessary, the charge generation layer 5 is subjected to
surface treatment by buffing and adjustment of the thickness thereof. On
the thus formed charge generation layer 5, a coating solution in which at
least one polyether compound and the binder agent are dissolved is coated
and dried, so that the charge transport layer 4 is formed. In the charge
generation layer 5, the same charge generating material as employed in the
above-mentioned photoconductive layer 2a can be used.
The thickness of the charge generation layer 5 is 5 .mu.m or less, more
preferably 2 .mu.m or less. It is preferable that the thickness of the
charge transport layer 4 be in the range of 3 to 50 .mu.m, more preferably
in the range of 5 to 20 .mu.m. When the charge generation layer 5 is
obtained by coating the dispersion in which finely-divided particles of
the charge generating material 3 is dispersed in an appropriate solvent
together with the binder agent, it is preferable that the amount of
finely-divided particles of the charge generating material 3 contained in
the charge generation layer 5 be in the range of 10 to 95 wt. %, more
preferably in the range of about 50 to 90 wt. %. It is preferable that the
amount of the polyether compound contained in the charge transport layer 4
be in the range of 10 to 95 wt. %, more preferably in the range of 30 to
90 wt. %.
The electrophotographic photoconductor shown in FIG. 7 can be obtained as
follows:
A coating solution in which the polyether compound and the binder agent are
dissolved is coated on the electroconductive support 1 and dried to form
the charge transport layer 4. On the thus formed charge transport layer 4,
a dispersion prepared by dispersing finely-divided particles of the charge
generating material 3 in the solvent, in which the binder agent is
dissolved when necessary, is coated by spray coating and dried to form the
charge generation layer 5 on the charge transport layer 4. The amount
ratio of components contained in the charge generation layer and charge
transport layer is the same as previously described in FIG. 6.
The electrophotographic photoconductor shown in FIG. 8 can be obtained by
forming a protective layer 6 on the charge generation layer 5 as obtained
in FIG. 7 by spray-coating of an appropriate resin solution. As a resin
employed in the protective layer 6, any of binder agents to be described
later can be used.
Specific examples of the electroconductive support 1 for the
electrophotographic photoconductor according to the present invention
include a metallic plate or foil made of aluminum, a plastic film on which
a metal such as aluminum is deposited, and a sheet of paper which has been
treated so as to be electroconductive.
Specific examples of the binder agent for use in the present invention are
condensation resins such as polyamide, polyurethane, polyester, epoxy
resin, polyketone and polycarbonate; and vinyl copolymers such as
polyvinylketone, polystyrene, poly-N-vinylcarbazole and polyacrylamide.
All the resins having insulating properties and adhesive force can be
employed.
Some plasticizers may be added to the above-mentioned binder agent, when
necessary. Examples of the plasticizer for use in the present invention
are halogenated paraffin, polybiphenyl chloride, dimethylnaphthalene and
dibutyl phthalate.
Furthermore, in the electrophotographic photoconductors according to the
present invention, an adhesive layer or barrier layer may be interposed
between the electroconductive support and the photoconductive layer when
necessary. Examples of the material for use in the adhesive layer or
barrier layer are polyamide, nitrocellulose and aluminum oxide. It is
preferable that the thickness of the adhesive layer or barrier layer be 1
.mu.m or less.
When copying is performed by use of the photoconductors according to the
present invention, the surface of the photoconductor is charged uniformly
in the dark to a predetermined polarity. The uniformly charged
photoconductor is exposed to a light image so that a latent electrostatic
image is formed on the photoconductor. The thus formed latent
electrostatic image is developed by a developer to a visible image, and
when necessary, the developed image can be transferred to a sheet of
paper. The electrophotographic photoconductors according to the present
invention have the advantages in that the photosensitivity is high and the
flexibility is improved.
Other features of this invention will become apparent in the course of the
following description of exemplary embodiments, which are given for
illustration of the invention and are not intended to be limiting thereof.
PREPARATION EXAMPLE 1-1
Preparation of 1,5-bis(4-iodophenoxy)-3-oxapentane
A mixture prepared by adding 3.08 g of sodium hydroxide and 40 ml of
n-butanol to 15.4 g of 4-iodophenol was refluxed. 2 ml of n-butanol
solution of 5.01 g of 1,5-dichloro-3-oxapentane was added dropwise to the
above prepared mixture over a period of 5 minutes.
After the completion of dropping, the reaction mixture was refluxed for 13
hours, and then cooled to room temperature.
The resulting mixture was diluted with methanol, so that crystals separated
out. These crystals were filtered off, washed with water and then
methanol, and dried under reduced pressure. As a result, 9.73 g of
colorless crystals was obtained in the form of needles.
These crystals were recrystallized from a mixed solvent of toluene and
n-hexane, so that 8.34 g of 1,5-bis(4-iodophenoxy)-3-oxapentane
precipitated as colorless crystals in the form of plates. The melting
point of the above compound was 139.5.degree. to 140.5.degree. C.
The results of the elemental analysis of the thus obtained compound were as
follows:
______________________________________
% C % H
______________________________________
Calculated 37.67 3.17
Found 37.59 2.92
______________________________________
The above calculation was based on the formula for
1,5-bis(4-iodophenoxy)-3-oxapentane of C.sub.16 H.sub.16 I.sub.2 O.sub.3.
FIG. 1 shows an infrared spectrum of 1,5-bis(4-iodophenoxy)-3-oxapentane,
taken by use of a KBr tablet.
PREPARATION EXAMPLE 1-2
Preparation of 1,5-bis(4'-iodobiphenylyl-4-oxy)-3-oxapentane
A mixture prepared by adding 0.45 g of sodium hydroxide and 20 ml of
n-butanol to 2.96 g of 4-(4-iodophenyl)phenol was refluxed. 1 ml of
n-butanol solution of 0.79 g of 1,5-dichloro-3-oxapentane was added
dropwise to the above prepared mixture over a period of 15 minutes.
After the completion of dropping, the reaction mixture was refluxed for 18
hours, and then cooled to room temperature, so that crystals separated
out. These crystals were filtered off, washed with water and then
methanol, and dried under reduced pressure. As a result, 2.30 g of
colorless crystals was obtained in the form of needles.
These crystals were washed with heated ethanol, so that 2.15 g of
1,5-bis(4'-iodobiphenylyl-4-oxy)-3-oxapentane precipitated as colorless
crystals in the form of needles. The melting point of the above compound
was 230.0.degree. to 231.0.degree. C.
The results of the elemental analysis of the thus obtained compound were as
follows:
______________________________________
% C % H
______________________________________
Calculated 50.77 3.66
Found 50.67 3.40
______________________________________
The above calculation was based on the formula for
1,5-bis(4'-iodobiphenylyl-4-oxy)-3-oxapentane of C.sub.28 H.sub.24 I.sub.2
O.sub.3.
FIG. 2 shows an infrared spectrum of
1,5-bis(4'-iodobiphenylyl-4-oxy)-3-oxapentane, taken by use of a KBr
tablet.
PREPARATION EXAMPLE 2-1
Synthesis of
1,5-bis{4'-N,N-bis(4-methylphenyl)-aminobiphenylyl-4-oxy}-3-oxapentane
--Polyether Compound No. 12 in Table 1
2.0 g of 1,5-bis(4'-iodobiphenylyl-4-oxy)-3-oxapentane prepared in
Preparation Example 1-2, 1.79 g of 4,4'-dimethyldiphenylamine, 1.25 g of
potassium carbonate and 0.25 g of copper particles were added to 20 ml of
nitrobenzene. This mixture was refluxed in a stream of nitrogen for 10
hours. After the mixture was cooled to room temperature, the resulting
insoluble material of the mixture was removed by filtration together with
Celite and nitrobenzene was removed therefrom.
The residue was extracted with toluene, washed with water and dried.
Thereafter, the thus obtained extract was concentrated under the reduced
pressure, so that oily dark brown material was obtained.
This oily material was subjected to column chromatography using silica gel
and toluene as a carrier and an eluting solution, respectively. The
product was recrystallized twice from a mixed solvent of ethyl acetate and
ethanol, so that 0.60 g of
1,5-bis{4'-N,N-bis(4-methylphenyl)-aminobiphenylyl-4-oxy}-3-oxapentane
precipitated as white crystals in the form of grains. The melting point of
the compound, namely the endothermic peak in accordance with TG-DSC, was
75.degree. C.
The results of the elemental analysis of the thus obtained compound were as
follows:
______________________________________
% C % H % N
______________________________________
Calculated 83.95 6.56 3.50
Found 83.86 6.72 3.38
______________________________________
The above calculation was based on the formula for
1,5-bis{4'-N,N-bis(4-methylphenyl)-aminobiphenylyl-4-oxy }-3-oxapentane of
C.sub.56 H.sub.52 N.sub.2 O.sub.3.
FIG. 3 shows an infrared spectrum of 1,5-bis
{4'-N,N-bis(4-methylphenyl)-aminobiphenylyl-4-oxy}-3-oxapentane,
(polyether compound No. 12 in Table 1) taken by use of a KBr tablet.
PREPARATION EXAMPLE 2-2
Synthesis of 1,5-bis(4-N,N-di-p-tolylaminophenoxy)-3-oxapentane --Polyether
Compound No. 4 in Table 1
5.10 g of 1,5-bis(4-iodophenoxy)-3-oxapentane prepared in Preparation
Example 1-1, 4.34 g of 4,4'-dimethyldiphenylamine, 4.15 g of potassium
carbonate and 0.83 g of copper particles were added to 60 m(of
nitrobenzene. This mixture was refluxed in a stream of nitrogen for 16
hours. After the mixture was cooled to room temperature, the resulting
insoluble material of the mixture was removed by filtration together with
Celite and nitrobenzene was removed therefrom.
The residue was extracted with toluene, washed with water and dried.
Thereafter, the thus obtained extract was concentrated under the reduced
pressure, so that oily dark brown material was obtained.
This oily material was subjected to column chromatography using silica gel
and toluene as a carrier and an eluting solution, respectively, so that
2.27 g of colorless oily
1,5-bis(4-N,N-di-p-tolylaminophenoxy)-3-oxapentane was obtained.
The results of the elemental analysis of the thus obtained compound were as
follows:
______________________________________
% C % H % N
______________________________________
Calculated 81.44 6.85 4.32
Found 81.22 6.78 4.33
______________________________________
The above calculation was based on the formula for
1,5-bis(4-N,N-di-p-tolylaminophenoxy)-3-oxapentane of C.sub.44 H.sub.44
N.sub.2 O.sub.3.
FIG. 4 shows an infrared spectrum of
1,5-bis(4-N,N-di-p-tolylaminophenoxy)-3-oxapentane (polyether compound No.
4 in Table 1), taken by use of a KBr tablet.
EXAMPLE 1
7.5 parts by weight of a bisazo compound having the following formula and
500 parts by weight of a 0.5% tetrahydrofuran solution of a polyester
resin (Trademark "Vylon 200" made by Toyobo Company, Ltd.) were dispersed
and ground in a ball mill. The thus prepared dispersion was coated on an
aluminum surface of an aluminum-deposited polyester film by a doctor
blade, and dried at room temperature, so that a charge generation layer
having a thickness of about 1 .mu.m was formed on the aluminum-deposited
polyester film.
##STR50##
One part by weight of
1,5-bis{4'-N,N-bis(4-methylphenyl)aminobiphenylyl-4-oxy}-3-oxapentane
(polyether compound No. 12 in Table 1) prepared in the above-mentioned
Preparation Example 2-1 was dissolved in a resin solution consisting of 1
part by weight of polycarbonate resin (Trademark "Panlite K-1300" made by
Teijin Limited.) and 8 parts by weight of tetrahydrofuran. This solution
was coated on the above formed charge generation layer by a doctor blade
and then dried at 80.degree. C. for 2 minutes and then at 120.degree. C.
for 5 minutes, so that a charge transport layer having a thickness of
about 20 .mu.m was formed on the charge generation layer. Thus a
two-layered type electrophotographic photoconductor No. 1 according to the
present invention was prepared.
EXAMPLE 2
76 parts by weight of Diane Blue (C.I. Pigment Blue 25, CI21180) serving as
a charge generating material, 1260 parts by weight of a 2% tetrahydrofuran
solution of a polyester resin (Trademark "Vylon 200" made by Toyobo
Company, Ltd.) and 3700 parts by weight of tetrahydrofuran were dispersed
and ground in a ball mill. The thus prepared dispersion was coated on an
aluminum surface of an aluminum-deposited polyester film by a doctor
blade, and dried at room temperature, so that a charge generation layer
having a thickness of about 1 .mu.m was formed on the aluminum-deposited
polyester film.
2 parts by weight of
1,5-bis{4'-N,N-bis(4-methylphenyl)aminobiphenylyl-4-oxy}-3-oxapentane
(polyether compound No. 12 in Table 1) prepared in the above-mentioned
Preparation Example 2-1, 2 parts by weight of polycarbonate resin
(Trademark "Panlite K-1300" made by Teijin Limited.) and 16 parts by
weight of tetrahydrofuran were mixed to form a solution. This solution was
coated on the above formed charge generation layer by a doctor blade and
then dried at 80.degree. C. for 2 minutes and then at 120.degree. C. for 5
minutes, so that a charge transport layer having a thickness of about 20
.mu.m was formed on the charge generation layer. Thus a two-layered type
electrophotographic photoconductor No. 2 according to the present
invention was prepared.
EXAMPLES 3 to 22
The procedure for preparation of the two-layered type electrophotographic
photoconductor No. 2 in Example 2 was repeated except that Diane Blue
serving as a charge generating material and the polyether compound No. 12
serving as a charge transporting material employed in Example 2 were
replaced by the respective charge generating materials and charge
transporting materials listed in the following Table 2, whereby
two-layered type electrophotographic photoconductors No. 3 to No. 22
according to the present invention were prepared.
TABLE 2
Charge Transporting Material (Polyether Photoconductor Charge
Generating Material Compound No.)
1
##STR51##
12
2
##STR52##
12
3
##STR53##
12
4
##STR54##
12
5
##STR55##
12
6
##STR56##
12
7 .beta. type
Copper Phthalocyanine 12
8
##STR57##
4
9
##STR58##
4 10 P-1 4 11 P-2 4 12 P-1 13 13 P-2 13 14 P-1 17 15 P-2 17 16 P-1
18 17 P-2 18 18 P-1 11 19 P-2 11 20 P-1 6 21 P-2
6
EXAMPLE 23
Selenium was vacuum-deposited on an aluminum plate having a thickness of
300 .mu.m, so that a charge generation layer having a thickness of about 1
.mu.m was formed on the aluminum plate.
2 parts by weight of
1,5-bis{4'-N,N-bis(4-methylphenyl)aminobiphenylyl-4-oxy}-3-oxapentane
(polyether compound No. 12 in Table 1) prepared in the above-mentioned
Preparation Example 2-1, 3 parts by weight of polyester resin (Trademark
"Polyester Adhesive 49000" made by Du Pont de Nemours, E.I. & Co.) and 45
parts by weight of tetrahydrofuran were mixed to form a solution. This
solution was coated on the above formed charge generation layer by a
doctor blade, dried at room temperature, and then dried under reduced
pressure, so that a charge transport layer with a thickness of about 10
.mu.m was formed on the charge generation layer. Thus a two-layered type
electrophotographic photoconductor No. 23 according to the present
invention was prepared.
EXAMPLE 24
The procedure for preparation of the two-layered electrophotographic
photoconductor No. 23 in Example 23 was repeated except that a charge
generation layer with a thickness of about 0.6 .mu.m was formed on the
same aluminum plate as employed in Example 23 by deposition of the
following perylene pigment instead of selenium, so that a two-layered
electrophotographic photoconductor No. 24 according to the present
invention was prepared.
##STR59##
EXAMPLE 25
A mixture of 1 part by weight of the same Diane Blue as employed in Example
2 and 158 parts by weight of tetrahydrofuran was dispersed and ground in a
ball mill to form a dispersion. To the thus formed dispersion, 12 parts by
weight of the polyether compound No. 12 in Table 1 and 18 parts by weight
of polyester resin (Trademark "Polyester Adhesive 49000" made by Du Pont
de Nemours, E.I. & Co.) were added to form a solution This solution was
coated on an aluminum-deposited polyester film by a doctor blade, and
dried at 100.degree. C. for 30 minutes, so that a photoconductive layer
having a thickness of about 16 .mu.m was formed on the electroconductive
support. Thus, an electrophotographic photoconductor No. 25 according to
the present invetnion was prepared.
EXAMPLE 26
2 parts by weight of 1,5-bis{4'-N,N-bis(4-methylphenyl)
aminobiphenylyl-4-oxy}-3-oxapentane (polyether compound No. 12 in Table 1)
prepared in the above-mentioned Preparation Example 2-1, 2 parts by weight
of polycarbonate resin (Trademark "Panlite K-1300" made by Teijin
Limited.) and 16 parts by weight of tetrahydrofuran were mixed to form a
solution. This solution was coated on the same aluminum surface of an
aluminum-deposited polyester film by a doctor blade and dried, so that a
charge transport layer with a thickness of about 20 .mu.m was formed on
the aluminum-deposited polyester film.
A mixture of 13.5 parts by weight of bisazo pigment (P-2), 5.4 parts by
weight of polyvinyl butyral (Trademark "XYHL" made by Union Carbide Japan
K.K.), 680 parts by weight of tetrahydrofuran and 1020 part by weight of
ethyl cellosolve was dispersed and ground in a ball mill. To this
dispersion, 1700 parts by Weight of additional ethyl cellosolve was added
to form a solution. This solution was coated on the above formed charge
transport layer by spray coating and dried at 100.degree. C. for 10
minutes, so that a charge generation layer having a thickness of about 0.2
.mu.m was formed on the charge transport layer.
A methanol - n-butanol based solution of a polyamide resin (Trademark
"CM-8000" made by Toray Silicone Co. Ltd.) was coated on the above formed
charge generation layer by spray coating and dried at 120.degree. C. for
30 minutes, so that a protective layer having a thickness of about 0.5
.mu.m was formed on the charge generation layer. Thus, an
electrophotographic photoconductor No. 25 according to the present
invention was prepared.
Each of the thus prepared electrophotographic photoconductors No. 1 through
No. 26 according to the present invention was charged negatively or
positively in the dark under application of -6 kV or +6 kV of corona
charge for 20 seconds, using a commercially available electrostatic
copying sheet testing apparatus ("Paper Analyzer Model SP-428" made by
Kawaguchi Electro Works Co., Ltd.). Then, each electrophotographic
photoconductor was allowed to stand in the dark for 20 seconds without
applying any charge thereto, and the surface potential Vpo (V) of the
photoconductor was measured. Each photoconductor was then illuminated by a
tungsten lamp in such a manner that the illuminance on the illuminated
surface of the photoconductor was 4.5 lux, and the exposure E.sub.1/2
(lux.sec) required to reduce the initial surface potential Vpo (V) to 1/2
the initial surface potential Vpo (V) was measured. The results are shown
in Table 3.
TABLE 3
______________________________________
Photoconductor No.
Vpo (V) E.sub.1/2 (lux .multidot. sec)
______________________________________
1 -1057 0.99
2 -1010 1.72
3 -980 1.40
4 -1210 1.18
5 -1330 2.30
6 -1060 0.99
7 -1110 2.01
8 -1310 1.80
9 -1290 1.70
10 -1020 1.45
11 -1270 1.12
12 -1180 0.82
13 -1220 1.20
14 -980 1.01
15 -1010 1.23
16 -1120 0.97
17 -1390 1.18
18 -1230 1.00
19 -990 1.21
20 -1020 0.90
21 -1270 1.10
22 -940 0.81
23 -720 2.40
24 -1370 3.21
25 +1290 2.40
26 +1130 0.97
______________________________________
The electrophotographic photoconductors according to the present invention
comprise a photoconductive layer comprising any of the above-mentioned
specific polyether compounds serving as an organic photoconductive
material, so that the resistance to heat and mechanical shocks of the
photoconductor can be improved as well as the photoconductive properties
thereof. Furthermore, the photoconductors according to the present
invention can be manufactured at low cost.
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